Homes in ZIP Code 33042

• 

  

  

  /46

  $899,000

  $150K PRICE DROP Under Contract

  • 3 Beds
  • 2 Baths
  • 1,144 Sq Ft

  288 Spanish Main Dr, Summerland Key, FL 33042

  MAJOR PRICE IMPROVEMENT -- AN EXCEPTIONAL VALUE FOR A BEAUTIFULLY UPDATED CUDJOE KEY CANAL-FRONT HOME! This updated 3-bedroom, 2-bath canal-front home on Cudjoe Key offers approximately 60 feet of concrete dockage directly behind the property, with plenty of room for your boat and convenient access to Gulf and Atlantic waters for fishing, diving, sandbar trips, and cruising the Lower Keys. The

  Richard Haskins Buy The Keys

  288 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  

  /52

  $2,300,000

  Sold Sep 12, 2025

  23086 Snapper Ln, Summerland Key, FL 33042

  • 4 Beds
  • 3 Baths
  • 2,586 Sq Ft
  • Built 1985

  Last Sold Summary

  • 8% Below List Price
  • $889/SF
  • 147 Days On Market

  Current Estimated Value $2,325,082

  Last Listing Agent Greg MacLaren Internet Realty of the Florida Keys

  23086 Snapper Ln, Summerland Key, FL 33042
• 

  

  

  /50

  Est $1,966,976

  Not Listed For Sale

  21025 Hamilton Ave, Summerland Key, FL 33042

  • 6 Beds
  • 3.5 Baths
  • 4,060 Sq Ft
  • Built 1983

  21025 Hamilton Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 47 Days On Market
• 

  

  

  /7

  $170,000

  • Land
  • 5,662 Sq Ft
  • $1,307,692 per Acre

  Lot 27 Dorn Rd, Torch Key, FL 33042

  If you love fishing, love the water, and hate the big crowds, this is the place for you! Upon arrival, the first thing you will notice is the peace and quiet. Easy access to the Gulf of America and Atlantic Ocean. This property is adjacent to my other listing which is owned by the same person. This would be an excellent opportunity to own a double lot on Big Torch Key! Adjacent property (blue

  Dylan Calhoun Luxe Properties

  Lot 27 Dorn Rd, Torch Key, FL 33042
• 

  

  

  /22

  $649,000

  Sold May 20, 2026

  19591 Navajo St, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,040 Sq Ft
  • Built 1994

  Last Sold Summary

  • 4% Below List Price
  • $624/SF
  • 25 Days On Market

  Current Estimated Value $657,742

  Last Listing Agent Mike Kane Internet Realty of the Florida Keys

  19591 Navajo St, Summerland Key, FL 33042
• 

  /2

  Est $1,045,974

  Not Listed For Sale

  152 Sugarloaf Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft
  • Built 1995

  152 Sugarloaf Dr, Summerland Key, FL 33042
• 

  

  /12

  $240,000

  Pending

  • 2 Beds
  • 1 Bath
  • 672 Sq Ft

  28177 Julia Ave, Little Torch Key, FL 33042

  Opportunity to purchase for land value in Little Torch Key. Large lot with existing mobile home on site that is not habitable. Property is being marketed as land only. Lot is zoned IS (Improved Subdivision District), which typically allows for single-family residential construction subject to Monroe County Land Development Code and applicable ROGO requirements. Conveniently located less than 5

  Maria Acosta Keller Williams Capital Realty

  28177 Julia Ave, Little Torch Key, FL 33042
• 

  

  /42

  $630,000

  Sold Jul 21, 2025

  92 Frazier Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2.5 Baths
  • 768 Sq Ft
  • Built 1980

  Last Sold Summary

  • 9% Below List Price
  • $820/SF
  • 43 Days On Market

  Current Estimated Value $563,620

  Last Listing Agent Stacey Pillari Berkshire Hathaway HomeServices Knight & Gardner Realty

  92 Frazier Ln, Summerland Key, FL 33042
• 

  

  /31

  Est $657,302

  Not Listed For Sale

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

  • 2 Beds
  • Built 1991

  701 Spanish Main Dr Unit 589, Cudjoe Key, FL 33042

  Last Sold Summary

  • 15 Days On Market
• 

  

  /72

  $595,000

  • 2 Beds
  • 2 Baths
  • 816 Sq Ft

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042

  Owner says ''Bring All Offers''Charming Coastal Retreat: 2 Bedroom, 2 Bath home with 35' concrete seawall. Nightly Rentals allowed.Welcome to your perfect getaway or investment opportunity! This delightful home built in 1993, offers 816 sq. ft. of comfortable living space, fully furnished and turn-key, making it an ideal choice for both relaxation and income generation. Step inside to discover a

  Lanny Gardner Bluescape Real Estate

  701 Spanish Main Dr Unit 604, Cudjoe Key, FL 33042
• 

  

  /29

  $1,400,000

  Sold Apr 24, 2026

  20841 8th Ave W, Cudjoe Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,872 Sq Ft
  • Built 1994

  Last Sold Summary

  • 10% Below List Price
  • $748/SF
  • 82 Days On Market

  Current Estimated Value $1,491,708

  Last Listing Agent Collin Tingle Coldwell Banker Schmitt Lower Keys (KW)

  20841 8th Ave W, Cudjoe Key, FL 33042
• 

  

  /15

  Est $740,460

  Not Listed For Sale

  16991 Shore Dr, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,134 Sq Ft
  • Built 1958

  16991 Shore Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 17 Days On Market
• 

  

  /62

  $2,599,000

  • 3 Beds
  • 2 Baths
  • 2,224 Sq Ft

  16843 E Point Dr, Summerland Key, FL 33042

  Welcome to your private waterfront retreat in the highly sought-after Southpoint neighborhood of Sugarloaf Key - where space, privacy and effortless access to the open water redefine the Lower Keys Lifestyle. Positioned along a crystal clear canal just moments from the Bay, this elevated residence offers over 2200 sq.ft of thoughtfully designed living space, featuring three spacious bedrooms and

  Suzanne Moore Truman & Co. (KW)

  16843 E Point Dr, Summerland Key, FL 33042
• 

  

  /16

  $785,000

  Sold Jul 25, 2025

  27384 Barbuda Ln, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,176 Sq Ft
  • Built 1993

  Last Sold Summary

  • 17% Below List Price
  • $668/SF
  • 125 Days On Market

  Current Estimated Value $849,533

  Last Listing Agent Lisa Carter Florida Keys Realty, Inc.

  27384 Barbuda Ln, Summerland Key, FL 33042
• 

  

  /56

  Est $1,799,871

  Not Listed For Sale

  20966 8th Ave W, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,166 Sq Ft
  • Built 1982

  20966 8th Ave W, Summerland Key, FL 33042

  Last Sold Summary

  • 31 Days On Market
• 

  

  /3

  $215,000

  • Land
  • 7,840 Sq Ft
  • $1,194,444 per Acre

  27334 Saint Lucie Ln, Big Pine, FL 33042

  Rare opportunity to own a piece of paradise in the heart of the Florida Keys. Located in the desirable Breezeswept Beach Estates community on Ramrod Key, this canal-front homesite offers the perfect blend of tranquility, natural beauty, and island living. The property benefits from a recorded Lot Line Adjustment that established the current buildable lot configuration, creating an excellent

  Gilberto Imery Gilvan Realty Corp

  27334 Saint Lucie Ln, Big Pine, FL 33042
• 

  

  /14

  $1,250,000

  Sold Aug 11, 2025

  365 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,400 Sq Ft
  • Built 1976

  Last Sold Summary

  • 6% Below List Price
  • $893/SF
  • 47 Days On Market

  Current Estimated Value $1,273,183

  Last Listing Agent Christopher Tanaka Coldwell Banker Schmitt RE Co.

  365 Pirates Rd, Summerland Key, FL 33042
• 

  

  /21

  Est $769,175

  Not Listed For Sale

  19570 Mayan St, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,424 Sq Ft
  • Built 1958

  19570 Mayan St, Summerland Key, FL 33042

  Last Sold Summary

  • 1 Day On Market
• 

  

  /50

  $1,349,000

  $100K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,820 Sq Ft

  845 Pirates Rd, Summerland Key, FL 33042

  Discover waterfront living in Jolly Roger Estates on Little Torch Key. This beautifully maintained 3 bedroom, 3 bathroom canal-front home offers quick boating access to open water, making it ideal for fishing and island adventures.Designed for the Florida Keys lifestyle, the property features a private pool, tiki hut, and spacious outdoor entertaining areas overlooking the canal. Boaters will

  Sandra Dolowy KeyIsle Realty

  845 Pirates Rd, Summerland Key, FL 33042
• 

  

  /17

  $16,000

  Sold Oct 28, 2025

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042

  • Land
  • 1.2 Acres
  • $13,333 per Acre

  Last Sold Summary

  • 23% Below List Price
  • 12 Days On Market

  Last Listing Agent Bobby Coe RE/MAX Keys Connection (KW)

  0 Budd Key Aly Unit 616603, Cudjoe Key, FL 33042
• 

  

  /73

  Est $1,101,368

  Not Listed For Sale

  103 Shore Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,128 Sq Ft
  • Built 1989

  103 Shore Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 24 Days On Market
• 

  

  /58

  $1,299,000

  $100K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,398 Sq Ft

  885 Hawksbill Ln, Summerland Key, FL 33042

  Recently updated canal-front home in highly desirable Upper Sugarloaf Key with direct boating access to the world famous Florida Keys back-country and Gulf of America. Located at 885 Hawksbill Lane, this waterfront property sits on a 6,120 sq ft lot and features a concrete seawall with boat davits, pavers and a heated swimming pool and spa completed in 2022. Enjoy canal and mangrove views plus

  Tommy Mack Coastal Collection Real Estate Inc.

  885 Hawksbill Ln, Summerland Key, FL 33042
• 

  

  /47

  $1,800,000

  Sold Apr 30, 2026

  23087 Sailfish Ln, Cudjoe Key, FL 33042

  • 3 Beds
  • 3.5 Baths
  • 2,100 Sq Ft
  • Built 1997

  Last Sold Summary

  • 10% Below List Price
  • $857/SF
  • 48 Days On Market

  Current Estimated Value $1,843,596

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  23087 Sailfish Ln, Cudjoe Key, FL 33042
• 

  

  /46

  Est $1,318,593

  Not Listed For Sale

  817 Grenada Ln, Summerland Key, FL 33042

  • 3 Beds
  • 2.5 Baths
  • 1,819 Sq Ft
  • Built 1993

  817 Grenada Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 25 Days On Market
• 

  

  /45

  $1,269,000

  • 2 Beds
  • 2 Baths
  • 1,100 Sq Ft

  116 Spanish Main Dr, Summerland Key, FL 33042

  Discover your personal island sanctuary in the heart of Cudjoe Key, where every day feels like Margaritaville. This stunning 2-bedroom, 2-bathroom single-family home has been thoughtfully updated to offer the ultimate waterfront lifestyle, featuring a sleek kitchen with a central island, 2025 updated appliances and two beautifully remodeled bathrooms. The interior glows with natural light,

  Tina Fingerman Beaches MLS

  116 Spanish Main Dr, Summerland Key, FL 33042
• 

  

  /59

  $900,000

  Sold Oct 31, 2025

  28550 Doubloon Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 2,371 Sq Ft
  • Built 1996

  Last Sold Summary

  • 18% Below List Price
  • $380/SF
  • 181 Days On Market

  Current Estimated Value $956,934

  Last Listing Agent Kelly Randin RE/MAX All Keys Real Estate

  28550 Doubloon Rd, Summerland Key, FL 33042
• 

  

  /41

  Est $1,102,693

  Not Listed For Sale

  366 Sawyer Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,390 Sq Ft
  • Built 1988

  366 Sawyer Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 4 Days On Market
• 

  

  /3

  $64,750

  • Land

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042

  ROGO Lot. Letter on hand from Monroe County granting 2 points

  Jenna Stauffer Ocean Sotheby's International Realty

  0 Lot 21 Aloha Dr, Little Torch Key, FL 33042
• 

  

  /47

  $1,100,000

  Sold Jun 12, 2026

  43 Venetian Way, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,250 Sq Ft
  • Built 1982

  Last Sold Summary

  • 17% Below List Price
  • $880/SF
  • 497 Days On Market

  Current Estimated Value $1,089,361

  Last Listing Agent Lori Cameron Buy The Keys

  43 Venetian Way, Summerland Key, FL 33042
• 

  

  /44

  Est $829,768

  Not Listed For Sale

  268 Spanish Main Dr, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 1,056 Sq Ft
  • Built 1979

  268 Spanish Main Dr, Summerland Key, FL 33042

  Last Sold Summary

  • 86 Days On Market
• 

  /2

  $249,000

  $50K PRICE DROP

  • Land
  • 6,098 Sq Ft
  • $1,778,571 per Acre

  28168 Julia Ave, Little Torch Key, FL 33042

  ROGO EXEMPT LOT! Build Now, No Waiting, Water Meter On Site, 6000 SF, Boat Ramp Within Walking Distance, Live The Dream. Single family home next door going on the market soon, buy both!

  Doug Addeo Regional Trust Corporation

  28168 Julia Ave, Little Torch Key, FL 33042
• 

  

  /5

  $328,000

  Sold Mar 27, 2026

  28292 Dorothy Ave, Summerland Key, FL 33042

  • 2 Beds
  • 2 Baths
  • 830 Sq Ft
  • Built 1975

  Last Sold Summary

  • $395/SF
  • 4 Days On Market

  Last Listing Agent Lauren Dunn Coldwell Banker Schmitt Islamorada

  28292 Dorothy Ave, Summerland Key, FL 33042
• 

  

  /36

  Est $1,006,504

  Not Listed For Sale

  21066 3rd Ave, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,245 Sq Ft
  • Built 1974

  21066 3rd Ave, Summerland Key, FL 33042

  Last Sold Summary

  • 326 Days On Market
• 

  

  /41

  $590,000

  $200K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,560 Sq Ft

  22920 Privateer Dr, Summerland Key, FL 33042

  Following a monumental $200,000 price drop, this rare waterfront opportunity is available at an unbeatable price point. Launch your boat from your backyard for world-class access to the Atlantic Ocean and Gulf of Mexico. Unlock instant equity with virtual additions in the photos and below-market pricing; there is significant room to secure this property way below market value after completing

  Jeff Shapiro Global Luxury Realty LLC

  22920 Privateer Dr, Summerland Key, FL 33042
• 

  

  /64

  $1,425,000

  Sold May 28, 2026

  17215 Bonita Ln E, Sugarloaf Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,528 Sq Ft
  • Built 2008

  Last Sold Summary

  • 5% Below List Price
  • $933/SF
  • 71 Days On Market

  Current Estimated Value $1,426,900

  Last Listing Agent Lisa Ferringo Coldwell Banker Schmitt Real Estate Co

  17215 Bonita Ln E, Sugarloaf Key, FL 33042
• 

  

  /27

  Est $875,737

  Not Listed For Sale

  27417 Cayman Ln, Summerland Key, FL 33042

  • 2 Beds
  • 1 Bath
  • 1,085 Sq Ft
  • Built 1975

  27417 Cayman Ln, Summerland Key, FL 33042

  Last Sold Summary

  • 274 Days On Market
• 

  

  /36

  $1,185,000

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft

  706 Caribbean Dr E, Summerland Key, FL 33042

  OVERSIZED GARAGE. WATERFRONT LIVING. Bring the boat, tackle, dive gear, kayaks, and all the Keys toys-there's room for everything at 706 Caribbean Drive East. With canal frontage, a 10,000-pound boat lift, and quick ocean access, this property is built for life on the water. The massive 1,188-square-foot garage below is a dream setup for serious boaters, offering space for storage, a workshop,

  Donna Pezzi Keller Williams Key West Compass Realty

  706 Caribbean Dr E, Summerland Key, FL 33042
• 

  

  /36

  $700,000

  Sold Jan 29, 2026

  24830 Park Dr, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 1,188 Sq Ft
  • Built 2015

  Last Sold Summary

  • 3% Below List Price
  • $589/SF
  • 7 Days On Market

  Current Estimated Value $725,929

  Last Listing Agent Patti Nickless Coldwell Banker Schmitt RE Co.

  24830 Park Dr, Summerland Key, FL 33042
• 

  

  /43

  Est $962,069

  Not Listed For Sale

  447 Pirates Rd, Summerland Key, FL 33042

  • 3 Beds
  • 2 Baths
  • 984 Sq Ft
  • Built 1991

  447 Pirates Rd, Summerland Key, FL 33042

  Last Sold Summary

  • 51 Days On Market
• 

  

  /64

  $1,499,000

  • 3 Beds
  • 3 Baths
  • 1,596 Sq Ft

  21007 4th Ave, Summerland Key, FL 33042

  Wake up to breathtaking Florida Keys sunrises from this exceptional oceanside waterfront home in Cudjoe Key. Offering 1,596 square feet of living space on an 8,920-square-foot lot, this CBS-built residence features 3 bedrooms and 3 bathrooms, + Office/beddroom,combining durability, comfort, and the relaxed island lifestyle you've been dreaming of.Designed for both everyday living and

  Diane Corliss Coldwell Banker Schmitt RE Co.

  21007 4th Ave, Summerland Key, FL 33042

Showing Results 401 - 440, Page 11 of 18